Penny was a shrewd attorney on the Southside, who happened to be in league with the Southside Serpents. However, she did not take monetary payments from fellow Serpent members, but instead, she demanded favors, which she expected in return should the time come. Penny also ran a secret drug trafficking operation, involving the transportation of what she refers to as "pancake mix", from the Southside of Riverdale to Greendale. She later went on to recruit Jughead Jones as her "transportation advisor", otherwise known as her drug-runner, until he exiled her to Greendale.

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Character Description

Penny is a wily backroom attorney that the Southside Serpents keep on retainer in case of run-ins with the law. She prefers that her clients pay her with favors, not cash, as Jughead finds out when he seeks her out to help with his father.[1]

Early Life

It is unknown exactly when Penny joined the Southside Serpents; however, the Serpents put her through college and she became a lawyer. She still remains a Serpent while behind the desk. Like all other Serpents, at some point in her young youthful years, she presumably completed the Serpents Initiation in order to join the Southside Serpents. During this time, Penny got involved with FP Jones, the extent of which remains unknown. A promise was made at some point from FP to Penny, which he failed to keep. This led to a falling out between the two.

Throughout Riverdale

In bed with the Snake Charmer

Jughead meeting with Penny, while she shows him her Serpent tattoo.

Jughead came by Penny's office to ask her for advice in his father's case, her office located in the back of a tattoo parlor. Penny explains to Jughead that she was and still is a Serpent, she reveals her Serpent tattoo on her left forearm and continues to tell him that they put her through college. Jughead reasons that having a lawyer of their own, on retainer, was clever. Penny mentions how his father used to brag about him being smart and this takes Jughead by surprise. Through mutual colleagues, the deal he was given is trash and Jughead pleads for her help with his case. She suggests that he get the victim's family to forgive FP in front of a judge in view of clemency, perhaps reducing his sentence to time served with parole. With services rendered, Jughead attempts to pay her, though she declines, asking that one day, maybe, he'll do her a favor.[2]

Penny contacted Jughead in the early hours of the morning to call in the favor that he owed her from when she offered him free consultation regarding FP's case.

Penny meeting up with Jughead at Pop's

The two of them met up at Pop's Chock'lit Shoppe, where Jughead refused to follow through on his end of the bargain. That is until Penny informed him that FP required further assistance. He was in the infirmary, Penny claimed. Supposedly, while in prison, FP was attacked by a few Ghoulies in the shower as a result of the deal that Jughead and his Northsider best friend made with Sheriff Keller to get the Ghoulies' higher-ups locked away. In order to broker a deal for FP's release, they needed money. Rich people don't sit in jail because money greases the wheels of justice, Penny surmised. Unfortunately, Jughead only had $18 to his name. In that case, Penny offered Jughead a one-time delivery job, where he would be required to pick up a crate on the Southside, and deliver it to an address in Greendale. As for the contents of the crate, Penny settled on calling it "pancake mix", in other words, drugs. She referred to Jughead as her transportation adviser. Should he agree, Penny would use his cut of the money for FP's case, to see if they could get him released earlier. Initially hesitant, after thinking it over, Jughead agreed to deliver the drugs. Penny then handed him the address before explaining that he needed to make the drop before midnight because Greendale is not a town you want to be in after such time. Lastly, the crate was rather large, so she advised him to get a ride as it wouldn't fit on his bike.

Penny blackmailing Jughead

The next day, Penny was confronted by Jughead after he discovered that she lied to him about FP getting jumped by the Ghoulies, though she preferred to look at it as if she gave him an incentive. She then showed Jughead video surveillance of him and Archie from the night before, entering the Greendale warehouse with the crate containing drugs. Holding the means to blackmail Jughead in her very hands, Penny informed him that his one-time drug delivery had become full time. Should he fail to comply or even raise his voice to her, Penny threatened to send the video to the Sheriff Station, which she imagined would break FP's heart given that Jughead would be arrested. He questioned why she was targeting him. Penny explained that FP made her a promise that he did not keep. So, as far as she was concerned, his depth was also Jughead's. Unfortunately for him, she was only just getting started.[3]

After successfully freeing FP from prison, Penny called Jughead from a booth in Pop's diner to arrange a meeting as they had business to discuss. However, Jughead refused to play along, having already told her that he was done. Although, should Jughead fail come as she had demanded, Penny threatened to have FP thrown back in jail.

Penny calling Jughead from Pop's

With no other options, Jughead showed up Pop's, but only to tell Penny that he wouldn't be held hostage by her. Having done his one favor as they previously negotiated, Jughead stated that he was out. However, Penny reminded him that he had debts to pay, and that their's was an on-going arrangement. In response, Jughead announced that he was about to have a sit-down with Mayor McCoy, who was actively working to stop the trafficking of drugs throughout Riverdale. With that, he threatened to reveal to the Mayor how Penny had taken over Clifford Blossom's operation. Unfortunately for Jughead, Penny was more than familiar with the law, stating that he would need proof to make an accusation like that stick, such as the surveillance video she has of him and Archie at the drop-off. However, as Jughead explained to Penny, an attack against him or his father, was an attack against all Serpents, which wouldn't bode over well with the gang. Just as Jughead stood from his seat and prepared to leave the diner, Penny mentioned his girlfriend, Betty Cooper who was quite fetching. "All snakes have a soft underbelly", Penny remarked. Betty so happened to be Jughead's.[4]

Kicked out of the Serpents

Southside Serpents taking Penny down

While at her warehouse, loading drugs into a crate for FP to later deliver, Penny heard a knock at the door. She assumed it was FP, arriving early. However, she was surprised to see that it was Jughead on the other side of the door. She then looked down, noticing the crowbar he had in his possession. Jughead explained that he was going to use it in case he had to pry the door open. With FP on his way, Penny asked Jughead to give her a hand with the drugs, which she assumed FP wouldn't be too happy about considering that he had taken Jughead's place because he didn't want him involved in drug trafficking. However, Jughead stated that he wasn't concerned with what his father had to say given that neither of them would be at the warehouse when FP arrived. Penny turned around to the sight of at least half a dozen Serpents wearing snake masks. "Is this supposed to scare me?", she asked. She then warned the young Serpents to stop what they were doing as they proceeded towards her, placing a black hood over her head and carrying her away.

Penny taken by the Serpents to Greendale

Penny was taken into Greendale, where the hood was then removed from over her head. Jughead explained that they had brought her to her new place of residence, as she had been banned from returning to the Southside. While they didn't care where she set up shop, it wasn't going to be in Riverdale or with the Serpents. If she wished to deal drugs and extort people, that would be done elsewhere, as long as Jughead had a say in the matter. Penny laughed in his face before pulling up the sleeve of her leather Serpents jacket to reveal her Serpents tattoo, stating that Serpent law prohibited them from hurting one of their own. Unfortunately for Penny, it was the time that she learns that her tattoo didn't make her a Serpent, especially since she hadn't been honoring their ways. She was then held down by Sweet Pea and Toni as Jughead pulled out a knife, and forcefully removed her tattoo with said knife, which was an excruciatingly painful process.[5]

Return of the Snake Charmer

Penny showing her scarred arm

After the head of General Augustus Pickens' statue was stolen from Pickens Park, Penny was called in by Tall Boy to help the Serpents combat the two week eviction notice from Sunnyside Trailer Park that they were given by Sheriff Keller and Mayor McCoy. At the Whyte Wyrm, the Serpents gathered around Penny as she told them how Jughead forcefully took her to Greendale and slice a chunk out of her arm where her Serpent tattoo used to be. He left her in Greendale, bleeding in a ditch. Nonetheless, Penny was still willing to help the Serpents. While the eviction notices that Tall Boy had shown her were legitimate, she could think of a number of ways that would stall the process by years. Her price, however, was blood for blood. An eye for an eye. She not only wanted her membership with the Serpents reinstated, but she wanted Jughead to be kicked out in her place. Though, for her final demand in exchange for her services, she wanted to carve off Jughead's tattoo with a dirty knife.[6]

An Alliance with the Ghoulies

Penny returns to Riverdale. She give Jughead a call. She sarcastically remarks that Riverdale burning to the ground is tragic. She suggests that they meet up to talk about it at his hangout by the docks. Should he refuse to meet up, Penny threatens to carve up Toni, who she has captured and restrained. When Toni tells Penny to go to hell, Penny threatens to cut out her tongue.

Penny teams up with Malachai and the Ghoulies

Jughead meets with Penny at his old hangout as planned. Toni, who is tied to the couch with rope, informs Jughead that Penny's not alone. She has apparently joined Malachai and the Ghoulies. She never goes anywhere with out back up now, not after what Jughead did to her. Besides, Penny and Malachai want to talk, but Jughead sees no reason to continue the conversation. He pulls out his knife and tells them that he's taking Toni. However, Malachai won't allow for it. With a taser in hand, he tells Jughead that he's been waiting to see him again for a long time. It seems that much like Penny, Jughead did not come alone. He called Cheryl, who armed with her bow and arrows, tells Malachai to stand down and requests that Toni be untied. Penny and Malachai comply, but Penny tells Jughead to remember that when his friends are dead, she tried to give him a chance to stop it. Jughead asks what Penny wants. She replies that she wants the Southside. There's money to be made in Riverdale. So, she partnered with the Ghoulies to sell drugs on the Southside. She makes Jughead one final offer. The Serpents leave Riverdale tonight or there will be a showdown at Pickens Park at dawn with the Ghoulies.

Penny, Malachai and the Ghoulies surround Jughead

It would later be revealed that Penny, Malachai and the Ghoulies were hired by Hiram Lodge. Jughead meets with them after making a deal with Hiram. If he hands himself over to them, then there will be no bloodshed tomorrow. Penny doesn't quite understand why getting Jughead out of the way is so important to Hiram than an all-out Serpent annihilation. Jughead is vastly outnumbered. He questions if Malachai needed that much backup because he's afraid of him. Malachai replies that the only thing scary is what they're going to do to Betty when they find her. Jughead punches Malachai in the face. The Ghoulies then jump him. Penny watches as the Ghoulies brutally attack Jughead. She remarks that while he is a true hero, his sacrifice was for nothing because come morning, Riverdale as Jughead knows it will cease to exist. The Ghoulies then hold Jughead down as Penny gets her pound of flesh by cutting off his Serpent tattoo.[7]

Welcome to the New Southside

On the other side of town, at the Whyte Wyrm, Hiram calls a meeting with all his accomplices i.e. Penny, Penelope, Claudius, Malachai and Sheriff Minetta. It's been months in the making but the time has finally arrived. Hiram welcomes them all to New Southside. Penelope asks about Hermione, who Hiram explains can't be privy to certain machinations now that she's mayor. But the plan remains the same. The prison will soon be up and operational, with Claudius' drugs running through it. "Like brother, like brother", Penny comments. Malachai and his Ghoulies will be their soldiers and dealers, with Penny troubleshooting. And hopefully, doing a better job than she did of killing Jughead, Hiram remarks. However, as Penny explains, he wasn't breathing when they left him. Penelope reminds Hiram that he promised her a brothel, which Hiram intends to make good on. As for Archie, Jughead, Betty and Veronica, they are not of concern as far as Hiram is concerned as steps have been taken to tear them apart.[8]

Physical Appearance

Penny is a young woman with straight blonde hair with bangs. She usually has her hair out loose, where small waves are shown. She has blue eyes and a slim body. As seen before on other members of the Southside Serpents, Penny previously had the gang's symbol of a double-headed serpent tattooed on her forearm, however this was removed by Jughead after she was expelled from the Serpents.

Personality

Penny appeared to be a kind woman when Jughead initially met her for consultation in regards to his father's case. However, it was later revealed that she is cold-hearted, manipulative, and calculated. This became evident to Jughead when she fooled him into a making a drug-run for her, from Riverdale to Greendale. She did this by fabricating a story of FP being attacked by the Ghoulies while in prison. She then used the surveillance video of Jughead at the drop off point to blackmail him into working for her as her "transportation advisor" (i.e. drug-runner).